Windsor Paint and Sip by Paint Juicy – Where History Meets Hilarity on the Hawkesbury

Step into the charm of yesteryear and splash your way into something fresh and fabulous at Windsor Paint and Sip by Paint Juicy. Nestled on the banks of the mighty Hawkesbury River and steeped in colonial stories, Windsor isn’t just a history lesson—it’s your next favourite night out.

We’re bringing the laughs, the colour, and a whole lot of cheeky fun to one of Australia’s oldest towns. Whether you're a lover of art, a fan of local wines, or just here for a good time, our paint and sip sessions are the perfect mix of creativity, social vibes, and that classic Paint Juicy energy.

What to Expect at Paint Juicy Windsor

Our events are nothing like a quiet gallery visit. Think party tunes, paintbrushes flying, drinks clinking, and everyone—from first-timers to crafty veterans—having an absolute blast.

• We supply everything you need: canvas, paints, brushes, apron
• Step-by-step guidance from our fun and fabulous hosts (zero pressure, max fun)
• Drinks and delicious eats available from our local venue partners
• A party atmosphere with great music, big laughs, and the freedom to go off-script on your canvas

It’s art with attitude, and you’ll walk away with a masterpiece—even if it’s more “abstract expressionism” than you planned.

A Town Built for Storytelling (and Painting It, Too)

Windsor is full of tales from Australia’s earliest days—convict-built buildings, cobbled streets, and colonial town squares. Now, it’s also the backdrop for modern-day fun with a twist of creativity.

• Start your day with a heritage walk through Thompson Square or a visit to the Hawkesbury Regional Museum
• Explore the Hawkesbury Regional Gallery for inspiration, then unleash your own inner artist with us that night
• Soak in the riverside scenery with a stroll along the Great River Walk, or go full adventure mode with kayaking, waterskiing or wakeboarding
• Catch a bite and a pint at a local pub before grabbing your seat at our next paint and sip session

This is a town where stories flow as easily as the river—and you’re about to add your own.

Perfect for All Occasions

Windsor Paint and Sip is where the past meets your party. Whatever you're celebrating (or even if you're not), our sessions are a hit for:

• Hens nights that want to blend a little elegance with a lot of laughter
• Birthdays big or small—everyone leaves with something better than a party bag
• Team building events that don’t involve trust falls or awkward icebreakers
• Date nights with a little paint and plenty of personality
• Local catch-ups, family fun, solo nights out, or something totally spontaneous

Whether you're bringing your crew or flying solo, we promise a fun night where everyone fits right in.

Make It a Windsor Getaway

There’s no need to rush off after your painting session. Windsor is made for exploring and relaxing.

• Stay in a cosy heritage B&B or riverside accommodation and turn your paint and sip into a full weekend escape
• Visit nearby wineries, local markets, and arts festivals like the Sydney Blues and Roots Festival in October
• Grab brunch the next morning and relive your paint party masterpieces over pancakes and coffee

You’ll be surprised just how much this history-rich town has going on—and how well a splash of colour suits it.

Time to Paint, Sip and Spin Some New Stories

Windsor Paint and Sip by Paint Juicy is where old-world charm meets new-school fun. We’re bringing life, laughter and a little creative chaos to one of NSW’s most picturesque historic towns. Come for the architecture, stay for the art—and leave with memories that last longer than your hangover.

Grab your crew, hold your paintbrush high, and let’s make a little history together, Paint Juicy style. See you at the easel, Windsor.